JP5144645B2 - 有機ｅｉｌ層を含むエレクトロルミネッセンス・デバイス - Google Patents
有機ｅｉｌ層を含むエレクトロルミネッセンス・デバイス Download PDFInfo
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- JP5144645B2 JP5144645B2 JP2009507710A JP2009507710A JP5144645B2 JP 5144645 B2 JP5144645 B2 JP 5144645B2 JP 2009507710 A JP2009507710 A JP 2009507710A JP 2009507710 A JP2009507710 A JP 2009507710A JP 5144645 B2 JP5144645 B2 JP 5144645B2
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- 239000000463 material Substances 0.000 claims description 190
- 125000003118 aryl group Chemical group 0.000 claims description 102
- -1 aromatic tertiary amine Chemical class 0.000 claims description 86
- 229910052757 nitrogen Inorganic materials 0.000 claims description 72
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 claims description 65
- 230000005525 hole transport Effects 0.000 claims description 62
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 claims description 60
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 claims description 60
- 125000001424 substituent group Chemical group 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 41
- 238000002347 injection Methods 0.000 claims description 34
- 239000007924 injection Substances 0.000 claims description 34
- 239000007983 Tris buffer Substances 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000003107 substituted aryl group Chemical group 0.000 claims description 23
- 125000004429 atom Chemical group 0.000 claims description 21
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 12
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 claims description 10
- LTUJKAYZIMMJEP-UHFFFAOYSA-N 9-[4-(4-carbazol-9-yl-2-methylphenyl)-3-methylphenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C(=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C)C(C)=C1 LTUJKAYZIMMJEP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000006267 biphenyl group Chemical group 0.000 claims description 8
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 claims description 8
- 150000002390 heteroarenes Chemical class 0.000 claims description 7
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- MEIBOBDKQKIBJH-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]-4-phenylcyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCC(CC1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 MEIBOBDKQKIBJH-UHFFFAOYSA-N 0.000 claims description 5
- OGOGJWNHOVWBPG-UHFFFAOYSA-N 4-n,4-n-bis[2,5-dimethyl-4-(n-(3-methylphenyl)anilino)phenyl]-2,5-dimethyl-1-n-(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC(=C(C)C=2)N(C=2C(=CC(=C(C)C=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C)C=2C(=CC(=C(C)C=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C)C)=C1 OGOGJWNHOVWBPG-UHFFFAOYSA-N 0.000 claims description 5
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 claims description 5
- NEGKJMRDAJYBPM-UHFFFAOYSA-N 9-(4-carbazol-9-ylphenyl)-3-n,3-n,6-n,6-n-tetraphenylcarbazole-3,6-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC(=CC=C3N(C=3C=CC(=CC=3)N3C4=CC=CC=C4C4=CC=CC=C43)C2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 NEGKJMRDAJYBPM-UHFFFAOYSA-N 0.000 claims description 5
- HDKRDRXHKYTCCZ-UHFFFAOYSA-N 9-(4-carbazol-9-ylphenyl)-n,n-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC(=CC=3)N3C4=CC=CC=C4C4=CC=CC=C43)C2=CC=1)C1=CC=CC=C1 HDKRDRXHKYTCCZ-UHFFFAOYSA-N 0.000 claims description 5
- SEZYVLIKGWIEBP-UHFFFAOYSA-N C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N2C3=CC=C(C=C3C3=CC=CC=C32)C=2C=CC=CC=2)C=2C=CC(=CC=2)N2C3=CC=C(C=C3C3=CC=CC=C32)C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 Chemical compound C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N2C3=CC=C(C=C3C3=CC=CC=C32)C=2C=CC=CC=2)C=2C=CC(=CC=2)N2C3=CC=C(C=C3C3=CC=CC=C32)C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 SEZYVLIKGWIEBP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005264 aryl amine group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- YANFTNKUUXOXRY-UHFFFAOYSA-N n,n-diphenyl-9-[4-[3-(n-phenylanilino)carbazol-9-yl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC(=CC=3)N3C4=CC=C(C=C4C4=CC=CC=C43)N(C=3C=CC=CC=3)C=3C=CC=CC=3)C2=CC=1)C1=CC=CC=C1 YANFTNKUUXOXRY-UHFFFAOYSA-N 0.000 claims description 5
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 claims description 4
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 claims description 4
- IWUKNGPIKBWAHE-UHFFFAOYSA-N 4-[1-[4-(diethylamino)-2-methylphenyl]-1-(4-methylphenyl)ethyl]-n,n-diethyl-3-methylaniline Chemical compound CC1=CC(N(CC)CC)=CC=C1C(C)(C=1C(=CC(=CC=1)N(CC)CC)C)C1=CC=C(C)C=C1 IWUKNGPIKBWAHE-UHFFFAOYSA-N 0.000 claims description 4
- KBXXZTIBAVBLPP-UHFFFAOYSA-N 4-[[4-(diethylamino)-2-methylphenyl]-(4-methylphenyl)methyl]-n,n-diethyl-3-methylaniline Chemical compound CC1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)N(CC)CC)C)C1=CC=C(C)C=C1 KBXXZTIBAVBLPP-UHFFFAOYSA-N 0.000 claims description 4
- WKXQCUSZXNBUPZ-UHFFFAOYSA-N 4-[[4-(diethylamino)phenyl]-diphenylmethyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)(C=1C=CC=CC=1)C1=CC=CC=C1 WKXQCUSZXNBUPZ-UHFFFAOYSA-N 0.000 claims description 4
- HPMDJLFQPKZBGR-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]-3-phenylpropyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C(CCC=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 HPMDJLFQPKZBGR-UHFFFAOYSA-N 0.000 claims description 4
- XHBAHUUUFQBVOL-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclopentyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 XHBAHUUUFQBVOL-UHFFFAOYSA-N 0.000 claims description 4
- VHGCFJXFDRSUNB-UHFFFAOYSA-N 4-methyl-n-[4-[4-methyl-1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1CC(C)CCC1(C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(N(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)C=C1 VHGCFJXFDRSUNB-UHFFFAOYSA-N 0.000 claims description 4
- FPMQTZDVSUPPCB-UHFFFAOYSA-N 9-(4-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 FPMQTZDVSUPPCB-UHFFFAOYSA-N 0.000 claims description 4
- DVNOWTJCOPZGQA-UHFFFAOYSA-N 9-[3,5-di(carbazol-9-yl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 DVNOWTJCOPZGQA-UHFFFAOYSA-N 0.000 claims description 4
- XCICDYGIJBPNPC-UHFFFAOYSA-N 9-[4-[3,5-bis(4-carbazol-9-ylphenyl)phenyl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=C(C=C(C=2)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 XCICDYGIJBPNPC-UHFFFAOYSA-N 0.000 claims description 4
- MLYXNJTVYLNKAW-UHFFFAOYSA-N c1ccc(cc1)N(c1ccccc1)c1ccc2n(-c3ccc(cc3)-n3c4ccc(cc4c4cc(ccc34)N(c3ccccc3)c3ccccc3)N(c3ccccc3)c3ccccc3)c3ccc(cc3c2c1)N(c1ccccc1)c1ccccc1 Chemical compound c1ccc(cc1)N(c1ccccc1)c1ccc2n(-c3ccc(cc3)-n3c4ccc(cc4c4cc(ccc34)N(c3ccccc3)c3ccccc3)N(c3ccccc3)c3ccccc3)c3ccc(cc3c2c1)N(c1ccccc1)c1ccccc1 MLYXNJTVYLNKAW-UHFFFAOYSA-N 0.000 claims description 4
- ZRCJJOYBRWQLER-UHFFFAOYSA-N n,n-diethyl-4-tritylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZRCJJOYBRWQLER-UHFFFAOYSA-N 0.000 claims description 4
- RYZPDEZIQWOVPJ-UHFFFAOYSA-N n-naphthalen-1-yl-n-[4-[4-[naphthalen-1-yl(naphthalen-2-yl)amino]phenyl]phenyl]naphthalen-2-amine Chemical group C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C4=CC=CC=C4C=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 RYZPDEZIQWOVPJ-UHFFFAOYSA-N 0.000 claims description 4
- JPDUPGAVXNALOL-UHFFFAOYSA-N 1-n,1-n,4-n,4-n-tetraphenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 JPDUPGAVXNALOL-UHFFFAOYSA-N 0.000 claims description 3
- YFTVWLKIADSAKW-UHFFFAOYSA-N 4-[2,6-dimethyl-4-(n-phenylanilino)phenyl]-3,5-dimethyl-n,n-diphenylaniline Chemical compound CC1=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=CC(C)=C1C(C(=C1)C)=C(C)C=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YFTVWLKIADSAKW-UHFFFAOYSA-N 0.000 claims description 3
- KNWWWMGCICBSSM-UHFFFAOYSA-N n,n-diphenyl-4-[4-[4-(n-phenylanilino)phenyl]phenyl]aniline Chemical group C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 KNWWWMGCICBSSM-UHFFFAOYSA-N 0.000 claims description 3
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 claims description 3
- YWKKLBATUCJUHI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=CC=C1 YWKKLBATUCJUHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 243
- 229910052799 carbon Inorganic materials 0.000 description 70
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 68
- 229910052741 iridium Inorganic materials 0.000 description 49
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 38
- 230000000903 blocking effect Effects 0.000 description 35
- RFVBBELSDAVRHM-UHFFFAOYSA-N 9,10-dinaphthalen-2-yl-2-phenylanthracene Chemical compound C1=CC=CC=C1C1=CC=C(C(C=2C=C3C=CC=CC3=CC=2)=C2C(C=CC=C2)=C2C=3C=C4C=CC=CC4=CC=3)C2=C1 RFVBBELSDAVRHM-UHFFFAOYSA-N 0.000 description 26
- 229910052751 metal Inorganic materials 0.000 description 25
- 239000002184 metal Substances 0.000 description 25
- 239000003446 ligand Substances 0.000 description 24
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 23
- 238000000034 method Methods 0.000 description 23
- 239000000758 substrate Substances 0.000 description 19
- 125000000623 heterocyclic group Chemical group 0.000 description 18
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 16
- 229910052782 aluminium Inorganic materials 0.000 description 15
- 150000002431 hydrogen Chemical class 0.000 description 15
- 125000005259 triarylamine group Chemical group 0.000 description 15
- 238000000151 deposition Methods 0.000 description 14
- 230000006870 function Effects 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 230000008021 deposition Effects 0.000 description 13
- 239000002019 doping agent Substances 0.000 description 13
- 125000001072 heteroaryl group Chemical group 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000004770 highest occupied molecular orbital Methods 0.000 description 12
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
- 150000004982 aromatic amines Chemical class 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 238000005286 illumination Methods 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 125000000547 substituted alkyl group Chemical group 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 150000001716 carbazoles Chemical class 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 125000000732 arylene group Chemical group 0.000 description 6
- 239000002274 desiccant Substances 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 229910052733 gallium Inorganic materials 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 6
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 6
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
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- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
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- 238000002310 reflectometry Methods 0.000 description 1
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- 125000006413 ring segment Chemical group 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
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- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
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- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
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- 230000003746 surface roughness Effects 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- ARZGWBJFLJBOTR-UHFFFAOYSA-N tetradecanamide Chemical compound CCCCCCCCCCCCCC(N)=O.CCCCCCCCCCCCCC(N)=O ARZGWBJFLJBOTR-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 238000004402 ultra-violet photoelectron spectroscopy Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/17—Carrier injection layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
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- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/412,544 US20070252516A1 (en) | 2006-04-27 | 2006-04-27 | Electroluminescent devices including organic EIL layer |
| US11/412,544 | 2006-04-27 | ||
| PCT/US2007/009022 WO2007127063A2 (fr) | 2006-04-27 | 2007-04-13 | DISPOSITIFS ÉLECTROLUMINESCENTS COMPRENANT UNE COUCHE d'injection d'électrons organique EIL |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009535812A JP2009535812A (ja) | 2009-10-01 |
| JP2009535812A5 JP2009535812A5 (fr) | 2010-06-03 |
| JP5144645B2 true JP5144645B2 (ja) | 2013-02-13 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2009507710A Active JP5144645B2 (ja) | 2006-04-27 | 2007-04-13 | 有機ｅｉｌ層を含むエレクトロルミネッセンス・デバイス |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20070252516A1 (fr) |
| EP (1) | EP2011178A2 (fr) |
| JP (1) | JP5144645B2 (fr) |
| KR (1) | KR101365424B1 (fr) |
| TW (1) | TW200746898A (fr) |
| WO (1) | WO2007127063A2 (fr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8647753B2 (en) * | 2005-10-12 | 2014-02-11 | Lg Display Co., Ltd. | Organic electroluminescence device |
| US9666826B2 (en) | 2005-11-30 | 2017-05-30 | Global Oled Technology Llc | Electroluminescent device including an anthracene derivative |
| JP4770699B2 (ja) * | 2005-12-16 | 2011-09-14 | ソニー株式会社 | 表示素子 |
| US20070252517A1 (en) * | 2006-04-27 | 2007-11-01 | Eastman Kodak Company | Electroluminescent device including an anthracene derivative |
| US9118020B2 (en) * | 2006-04-27 | 2015-08-25 | Global Oled Technology Llc | Electroluminescent devices including organic eil layer |
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| US7597967B2 (en) * | 2004-12-17 | 2009-10-06 | Eastman Kodak Company | Phosphorescent OLEDs with exciton blocking layer |
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- 2006-04-27 US US11/412,544 patent/US20070252516A1/en not_active Abandoned
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- 2007-04-13 EP EP07775264A patent/EP2011178A2/fr not_active Withdrawn
- 2007-04-13 KR KR1020087026253A patent/KR101365424B1/ko active IP Right Grant
- 2007-04-13 JP JP2009507710A patent/JP5144645B2/ja active Active
- 2007-04-26 TW TW096114731A patent/TW200746898A/zh unknown
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|---|---|
| EP2011178A2 (fr) | 2009-01-07 |
| US20070252516A1 (en) | 2007-11-01 |
| KR20090007734A (ko) | 2009-01-20 |
| JP2009535812A (ja) | 2009-10-01 |
| WO2007127063A3 (fr) | 2008-03-13 |
| WO2007127063A2 (fr) | 2007-11-08 |
| TW200746898A (en) | 2007-12-16 |
| KR101365424B1 (ko) | 2014-02-26 |
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